data_6CE # _chem_comp.id 6CE _chem_comp.name "5'-S-[(S)-hydroxy{[2-(1H-indol-3-yl)ethyl]amino}phosphoryl]-5'-thioguanosine" _chem_comp.type NON-POLYMER _chem_comp.pdbx_type HETAIN _chem_comp.formula "C20 H24 N7 O6 P S" _chem_comp.mon_nstd_parent_comp_id ? _chem_comp.pdbx_synonyms TrpGMPS _chem_comp.pdbx_formal_charge 0 _chem_comp.pdbx_initial_date 2016-03-10 _chem_comp.pdbx_modified_date 2020-06-17 _chem_comp.pdbx_ambiguous_flag N _chem_comp.pdbx_release_status REL _chem_comp.pdbx_replaced_by ? _chem_comp.pdbx_replaces ? _chem_comp.formula_weight 521.487 _chem_comp.one_letter_code ? _chem_comp.three_letter_code 6CE _chem_comp.pdbx_model_coordinates_details ? _chem_comp.pdbx_model_coordinates_missing_flag N _chem_comp.pdbx_ideal_coordinates_details Corina _chem_comp.pdbx_ideal_coordinates_missing_flag N _chem_comp.pdbx_model_coordinates_db_code 5IPC _chem_comp.pdbx_subcomponent_list ? _chem_comp.pdbx_processing_site RCSB # # loop_ _chem_comp_atom.comp_id _chem_comp_atom.atom_id _chem_comp_atom.alt_atom_id _chem_comp_atom.type_symbol _chem_comp_atom.charge _chem_comp_atom.pdbx_align _chem_comp_atom.pdbx_aromatic_flag _chem_comp_atom.pdbx_leaving_atom_flag _chem_comp_atom.pdbx_stereo_config _chem_comp_atom.model_Cartn_x _chem_comp_atom.model_Cartn_y _chem_comp_atom.model_Cartn_z _chem_comp_atom.pdbx_model_Cartn_x_ideal _chem_comp_atom.pdbx_model_Cartn_y_ideal _chem_comp_atom.pdbx_model_Cartn_z_ideal _chem_comp_atom.pdbx_component_atom_id _chem_comp_atom.pdbx_component_comp_id _chem_comp_atom.pdbx_ordinal 6CE C8 C1 C 0 1 N N R -29.695 6.862 -28.436 3.475 -1.740 0.964 C8 6CE 1 6CE C5 C2 C 0 1 N N N -29.201 4.198 -25.900 0.492 -0.364 2.283 C5 6CE 2 6CE C6 C3 C 0 1 N N S -28.747 5.213 -26.949 1.247 -0.753 1.011 C6 6CE 3 6CE C2 C4 C 0 1 N N N -32.184 7.803 -24.241 -5.568 1.834 0.165 C2 6CE 4 6CE C4 C5 C 0 1 Y N N -34.079 8.592 -22.481 -7.484 0.111 -0.469 C4 6CE 5 6CE NE2 N1 N 0 1 N N N -32.318 5.376 -23.723 -3.138 1.681 0.430 NE2 6CE 6 6CE P1 P1 P 0 1 N N N -31.501 3.865 -23.958 -2.110 0.406 0.815 P1 6CE 7 6CE O2 O1 O 0 1 N N N -30.294 3.802 -23.049 -2.919 -0.700 1.661 O2 6CE 8 6CE O3 O2 O 0 1 N N N -32.524 2.767 -23.802 -1.594 -0.206 -0.430 O3 6CE 9 6CE S4 S1 S 0 1 N N N -30.927 3.840 -25.947 -0.488 1.131 1.972 S4 6CE 10 6CE C7 C6 C 0 1 N N S -29.490 6.547 -26.954 1.990 -2.085 1.229 C7 6CE 11 6CE C9 C7 C 0 1 N N R -28.859 5.787 -29.110 3.362 -0.446 0.119 C9 6CE 12 6CE O10 O3 O 0 1 N N N -28.939 4.669 -28.250 2.238 0.243 0.706 O10 6CE 13 6CE N11 N2 N 0 1 Y N N -29.378 5.435 -30.435 4.581 0.358 0.240 N11 6CE 14 6CE C12 C8 C 0 1 Y N N -30.664 5.225 -30.768 4.783 1.390 1.109 C12 6CE 15 6CE N13 N3 N 0 1 Y N N -30.754 4.927 -32.087 5.981 1.873 0.940 N13 6CE 16 6CE C14 C9 C 0 1 Y N N -29.499 4.935 -32.587 6.605 1.180 -0.041 C14 6CE 17 6CE C15 C10 C 0 1 Y N N -28.598 5.264 -31.485 5.720 0.207 -0.489 C15 6CE 18 6CE N16 N4 N 0 1 N N N -27.261 5.353 -31.667 6.119 -0.639 -1.492 N16 6CE 19 6CE C17 C11 C 0 1 N N N -26.775 5.115 -32.905 7.358 -0.526 -2.039 C17 6CE 20 6CE N18 N5 N 0 1 N N N -27.537 4.813 -33.978 8.226 0.380 -1.643 N18 6CE 21 6CE C19 C12 C 0 1 N N N -28.868 4.699 -33.898 7.930 1.250 -0.665 C19 6CE 22 6CE N20 N6 N 0 1 N N N -25.327 5.203 -33.090 7.717 -1.390 -3.039 N20 6CE 23 6CE O21 O4 O 0 1 N N N -29.551 4.428 -34.919 8.744 2.087 -0.307 O21 6CE 24 6CE O22 O5 O 0 1 N N N -28.702 7.526 -26.252 1.532 -3.070 0.300 O22 6CE 25 6CE O23 O6 O 0 1 N N N -29.276 8.169 -28.847 4.116 -2.780 0.223 O23 6CE 26 6CE C1 C13 C 0 1 N N N -31.589 6.613 -23.490 -4.277 1.215 -0.373 C1 6CE 27 6CE C3 C14 C 0 1 Y N N -33.598 8.133 -23.806 -6.736 1.356 -0.659 C3 6CE 28 6CE C13 C15 C 0 1 Y N N -34.744 8.104 -24.600 -7.288 1.990 -1.705 C13 6CE 29 6CE C22 C16 C 0 1 Y N N -35.536 8.783 -22.621 -8.479 0.100 -1.463 C22 6CE 30 6CE N23 N7 N 0 1 Y N N -35.851 8.476 -23.891 -8.329 1.253 -2.201 N23 6CE 31 6CE C24 C17 C 0 1 Y N N -33.439 8.826 -21.276 -7.391 -0.949 0.435 C24 6CE 32 6CE C25 C18 C 0 1 Y N N -34.212 9.257 -20.200 -8.264 -1.996 0.345 C25 6CE 33 6CE C26 C19 C 0 1 Y N N -35.591 9.441 -20.315 -9.244 -2.014 -0.639 C26 6CE 34 6CE C27 C20 C 0 1 Y N N -36.261 9.210 -21.515 -9.362 -0.972 -1.532 C27 6CE 35 6CE H1 H1 H 0 1 N N N -30.754 6.705 -28.690 4.003 -1.549 1.899 H1 6CE 36 6CE H2 H2 H 0 1 N N N -28.649 3.261 -26.064 -0.171 -1.178 2.576 H2 6CE 37 6CE H3 H3 H 0 1 N N N -28.958 4.597 -24.904 1.205 -0.170 3.084 H3 6CE 38 6CE H4 H4 H 0 1 N N N -27.678 5.416 -26.789 0.548 -0.849 0.180 H4 6CE 39 6CE H5 H5 H 0 1 N N N -32.194 7.569 -25.316 -5.709 1.535 1.204 H5 6CE 40 6CE H6 H6 H 0 1 N N N -31.548 8.683 -24.063 -5.502 2.921 0.106 H6 6CE 41 6CE H7 H7 H 0 1 N N N -32.872 5.526 -24.542 -3.453 2.156 1.262 H7 6CE 42 6CE H8 H8 H 0 1 N N N -30.361 3.041 -22.485 -3.287 -0.368 2.491 H8 6CE 43 6CE H9 H9 H 0 1 N N N -30.470 6.420 -26.470 1.855 -2.434 2.253 H9 6CE 44 6CE H10 H10 H 0 1 N N N -27.820 6.138 -29.196 3.162 -0.686 -0.925 H10 6CE 45 6CE H11 H11 H 0 1 N N N -31.500 5.285 -30.086 4.061 1.751 1.826 H11 6CE 46 6CE H12 H12 H 0 1 N N N -26.652 5.587 -30.910 5.511 -1.323 -1.815 H12 6CE 47 6CE H13 H13 H 0 1 N N N -24.927 5.041 -33.992 7.092 -2.065 -3.344 H13 6CE 48 6CE H14 H14 H 0 1 N N N -24.736 5.425 -32.314 8.597 -1.326 -3.441 H14 6CE 49 6CE H15 H15 H 0 1 N N N -28.615 7.269 -25.342 2.006 -3.912 0.354 H15 6CE 50 6CE H16 H16 H 0 1 N N N -29.811 8.824 -28.414 4.131 -3.634 0.676 H16 6CE 51 6CE H17 H17 H 0 1 N N N -30.549 6.475 -23.819 -4.343 0.128 -0.314 H17 6CE 52 6CE H18 H18 H 0 1 N N N -31.607 6.833 -22.412 -4.135 1.514 -1.412 H18 6CE 53 6CE H19 H19 H 0 1 N N N -34.755 7.823 -25.643 -6.957 2.940 -2.099 H19 6CE 54 6CE H20 H20 H 0 1 N N N -36.776 8.515 -24.268 -8.881 1.507 -2.957 H20 6CE 55 6CE H21 H21 H 0 1 N N N -32.374 8.679 -21.173 -6.631 -0.942 1.202 H21 6CE 56 6CE H22 H22 H 0 1 N N N -33.732 9.454 -19.253 -8.192 -2.816 1.044 H22 6CE 57 6CE H23 H23 H 0 1 N N N -36.152 9.770 -19.453 -9.927 -2.849 -0.697 H23 6CE 58 6CE H24 H24 H 0 1 N N N -37.328 9.361 -21.584 -10.131 -0.993 -2.290 H24 6CE 59 # # loop_ _chem_comp_bond.comp_id _chem_comp_bond.atom_id_1 _chem_comp_bond.atom_id_2 _chem_comp_bond.value_order _chem_comp_bond.pdbx_aromatic_flag _chem_comp_bond.pdbx_stereo_config _chem_comp_bond.pdbx_ordinal 6CE O21 C19 DOUB N N 1 6CE N18 C19 SING N N 2 6CE N18 C17 DOUB N N 3 6CE C19 C14 SING N N 4 6CE N20 C17 SING N N 5 6CE C17 N16 SING N N 6 6CE C14 N13 SING Y N 7 6CE C14 C15 DOUB Y N 8 6CE N13 C12 DOUB Y N 9 6CE N16 C15 SING N N 10 6CE C15 N11 SING Y N 11 6CE C12 N11 SING Y N 12 6CE N11 C9 SING N N 13 6CE C9 C8 SING N N 14 6CE C9 O10 SING N N 15 6CE O23 C8 SING N N 16 6CE C8 C7 SING N N 17 6CE O10 C6 SING N N 18 6CE C7 C6 SING N N 19 6CE C7 O22 SING N N 20 6CE C6 C5 SING N N 21 6CE S4 C5 SING N N 22 6CE S4 P1 SING N N 23 6CE C13 N23 SING Y N 24 6CE C13 C3 DOUB Y N 25 6CE C2 C3 SING N N 26 6CE C2 C1 SING N N 27 6CE P1 O3 DOUB N N 28 6CE P1 NE2 SING N N 29 6CE P1 O2 SING N N 30 6CE N23 C22 SING Y N 31 6CE C3 C4 SING Y N 32 6CE NE2 C1 SING N N 33 6CE C22 C4 DOUB Y N 34 6CE C22 C27 SING Y N 35 6CE C4 C24 SING Y N 36 6CE C27 C26 DOUB Y N 37 6CE C24 C25 DOUB Y N 38 6CE C26 C25 SING Y N 39 6CE C8 H1 SING N N 40 6CE C5 H2 SING N N 41 6CE C5 H3 SING N N 42 6CE C6 H4 SING N N 43 6CE C2 H5 SING N N 44 6CE C2 H6 SING N N 45 6CE NE2 H7 SING N N 46 6CE O2 H8 SING N N 47 6CE C7 H9 SING N N 48 6CE C9 H10 SING N N 49 6CE C12 H11 SING N N 50 6CE N16 H12 SING N N 51 6CE N20 H13 SING N N 52 6CE N20 H14 SING N N 53 6CE O22 H15 SING N N 54 6CE O23 H16 SING N N 55 6CE C1 H17 SING N N 56 6CE C1 H18 SING N N 57 6CE C13 H19 SING N N 58 6CE N23 H20 SING N N 59 6CE C24 H21 SING N N 60 6CE C25 H22 SING N N 61 6CE C26 H23 SING N N 62 6CE C27 H24 SING N N 63 # # loop_ _pdbx_chem_comp_descriptor.comp_id _pdbx_chem_comp_descriptor.type _pdbx_chem_comp_descriptor.program _pdbx_chem_comp_descriptor.program_version _pdbx_chem_comp_descriptor.descriptor 6CE SMILES ACDLabs 12.01 "C3(C(C(CSP(NCCc2c1ccccc1nc2)(=O)O)OC3n4cnc5c4NC(=NC5=O)N)O)O" 6CE InChI InChI 1.03 "InChI=1S/C20H24N7O6PS/c21-20-25-17-14(18(30)26-20)23-9-27(17)19-16(29)15(28)13(33-19)8-35-34(31,32)24-6-5-10-7-22-12-4-2-1-3-11(10)12/h1-4,7,9,13,15-16,19,22,28-29H,5-6,8H2,(H2,24,31,32)(H3,21,25,26,30)/t13-,15-,16-,19-/m1/s1" 6CE InChIKey InChI 1.03 WJQUHDQKVRSGDO-NVQRDWNXSA-N 6CE SMILES_CANONICAL CACTVS 3.385 "NC1=NC(=O)c2ncn([C@@H]3O[C@H](CS[P](O)(=O)NCCc4c[nH]c5ccccc45)[C@@H](O)[C@H]3O)c2N1" 6CE SMILES CACTVS 3.385 "NC1=NC(=O)c2ncn([CH]3O[CH](CS[P](O)(=O)NCCc4c[nH]c5ccccc45)[CH](O)[CH]3O)c2N1" 6CE SMILES_CANONICAL "OpenEye OEToolkits" 2.0.4 "c1ccc2c(c1)c(c[nH]2)CCNP(=O)(O)SC[C@@H]3[C@H]([C@H]([C@@H](O3)n4cnc5c4NC(=NC5=O)N)O)O" 6CE SMILES "OpenEye OEToolkits" 2.0.4 "c1ccc2c(c1)c(c[nH]2)CCNP(=O)(O)SCC3C(C(C(O3)n4cnc5c4NC(=NC5=O)N)O)O" # # loop_ _pdbx_chem_comp_identifier.comp_id _pdbx_chem_comp_identifier.type _pdbx_chem_comp_identifier.program _pdbx_chem_comp_identifier.program_version _pdbx_chem_comp_identifier.identifier 6CE "SYSTEMATIC NAME" ACDLabs 12.01 "5'-S-[(S)-hydroxy{[2-(1H-indol-3-yl)ethyl]amino}phosphoryl]-5'-thioguanosine" 6CE "SYSTEMATIC NAME" "OpenEye OEToolkits" 2.0.4 "[(2~{S},3~{S},4~{R},5~{R})-5-(2-azanyl-6-oxidanylidene-3~{H}-purin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methylsulfanyl-~{N}-[2-(1~{H}-indol-3-yl)ethyl]phosphonamidic acid" # # loop_ _pdbx_chem_comp_audit.comp_id _pdbx_chem_comp_audit.action_type _pdbx_chem_comp_audit.date _pdbx_chem_comp_audit.processing_site 6CE "Create component" 2016-03-10 RCSB 6CE "Initial release" 2017-03-15 RCSB 6CE "Modify synonyms" 2020-06-05 PDBE # _pdbx_chem_comp_synonyms.ordinal 1 _pdbx_chem_comp_synonyms.comp_id 6CE _pdbx_chem_comp_synonyms.name TrpGMPS _pdbx_chem_comp_synonyms.provenance ? _pdbx_chem_comp_synonyms.type ? ##